Diethyl Sulfate → HCID 10559488, compound

HRID 1885304Notes

Reaction equation

HRID 1885304 reaction equation
Cl.[CH2:2]([O:4][C:5]([C@@H:7]1[CH2:11][C@@H:10]([OH:12])[CH2:9][NH:8]1)=[O:6])[CH3:3].C(=O)([O-])[O-].[K+].[K+].S(OCC)(O[CH2:23][CH3:24])(=O)=O>C(Cl)(Cl)Cl>[CH2:2]([O:4][C:5]([C@@H:7]1[CH2:11][C@@H:10]([OH:12])[CH2:9][N:8]1[CH2:23][CH3:24])=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 12709304Ethyl trans-4-hydroxy-L-prolinate hydrochloride

Product 1

HCID 10559488HCID 10559488, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 10.0 g of (2S,4R)-2-ethoxycarbonyl-4-hydroxy pyrrolidine hydrochloride, 15.5 g of potassium carbonate and 50 ml of chloroform, 9.46 g of diethyl sulfate were dropwise added. At 40° C., the mixture was stirred for 4 hours and then allowed to cool, washed with water, added with an aqueous dilute HCl solution and the formed aqueous layer was separated. This aqueous layer was neutralized with potassium carbonate, extracted with chloroform and the extract was washed with water, dried and concentrated under reduced pressure to obtain (2S,4R)-2-ethoxycarbonyl-N-ethyl4-hydroxy pyrrolidine as an oily product. Yield 8.15 g.

Workup

  1. additionwere dropwise added
  2. temperatureto cool
  3. washwashed with water
  4. additionadded with an aqueous dilute HCl solution
  5. customthe formed aqueous layer was separated
  6. extractionextracted with chloroform
  7. washthe extract was washed with water
  8. customdried
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aac68d835d6145fbae98cd5bdf83f252
Source dataset
uspto-grants-1992_09
Patent number
US05143935

Reaction notes

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